Lucky Bastard 40: Going Out With A Bang
Starring Hailee Steinfeld, Victoria Justice, Bailee Madison, Madison Pettis, Natalie Alyn Lind, Sabrina Carpenter, Joey King, Anna Kendrick, Dove Cameron, Paris Berelc, Kelli Berglund, and Olivia Holt
Codes: MF, FF, MF, MFFFF, Oral, Anal, Creampie, Titty Fuck, Facial, ATM, Scissoring,
Written by MiamiLyfe
Disclaimer: The following is completely fictional and it is nothing but pure fantasy







"Oh my god, yes! Ahhhh!" Hailee Steinfeld cried in pleasure from our bed for the second time this morning. She'd come home late last night after several weeks away on the set of her latest project, and after a good night of restful sleep, we had spent the morning blissfully celebrating her return. I had woken her several soft kisses along her shoulder and neck. She rolled over and kissed me back. We continued making out until I flung the bedding off us and moved down her body. I had spent the last 30 minutes with my face and fingers buried between her amazing long shapely legs, and I didn't plan on stopping any time soon.

"Ugghaaahhhh," she gripped the sheets for dear life as the rest of her body quivered. My lips remained locked around her clit as she rode out her orgasm. "You're not going to let up, are you?" she asked breathlessly.

"You're going to have to beg to get me to stop," I told her. "I'm enjoying this way too much."

The two of us were in a good place, a very good place. Though we are still technically in an open relationship, neither had used it since Haiz was in Atlanta and I was in Vancouver. The only exceptions were when Ella Hunt came home for a threesome with Hailee and me at the Dickinson Season 3 wrap party and then again the night of Dickinson's Season 3 premiere. It's not that I did not have any other opportunities for other hookups, but rather because of a lack of desire on my part to act on those opportunities. The truth was I had known I was happy with it being just Hailee and me for a while. Going back to COVID lockdown in LA, I knew then that she was the only one that I wanted. Our threesome with Bailee Madison when restrictions began to lift had really highlighted that in my mind. That's why a few days after that hookup, I purchased an engagement ring which I had been hiding in an office safe. That was over two years ago.

Two and a half months ago, I had dinner alone with her parents, and then six weeks ago, I proposed on a trip to Miami while she had a few days off from shooting Hawkeye Season 2 in Atlanta. After being up most of the night, I suggested staying up to watch the sunrise over Biscayne Bay. We sat outside and watched as the sun rose over the water. It was there that I proposed. She accepted and, after taking a few pictures, we hurried back to our hotel room. Later that night, after we spent several hours celebrating our new engagement by fucking until we were both too dehydrated to continue, we had room service and talked. We decided that we would go exclusive with one exception. We decided to have one final day to get whatever desires we might have out of our system. One 24 hour period starting with an engagement party/house part we were throwing with only friends. No family or relatives are allowed at this part for obvious reasons. We can have whatever final hookup we want during that time, and afterward, it would be just the two of us going forward.

The next day the two of us spent most of the day in our room on our phones as we started letting people know of our engagement. Three weeks later, we had our nice mature engagement party with family members and close personal friends. And now today was the morning of our friends-only engagement party, which was going to be just a big rager of a house party. As part of our agreement to not make for the chance of awkward/uncomfortable situations, we agreed that Hailee would spend the night at a hotel, and she would not show up back at my place until 5pm tomorrow.

"Fuck, Hailee," I groaned as we were now doing it doggy style. I did not need to do much with how Hailee moved her ass back to me and rotated her hips. There was not much I could do to improve how it felt as she fucked herself back on my dick. I let her keep going until finally, I could not take it anymore. I was going to cum soon, and from the way she was moaning, I knew she was close too. I flipped Hailee over onto her back, and I got on top of her. We looked into each other's eyes as we came simultaneously, with me exploding inside of her.

After we came, Hailee and I continued to kiss and make out for several minutes. After our lips broke apart, I continued kissing her. I did so along her neck and collarbone as I moved to lay next to her. Finally, we were just both lying on our sides facing one another.

"You sure you want to go through with this party? We could still call the whole thing off. We could just stay in bed and fuck one another instead," I offered.

"That's tempting," Hailee admitted. "But I think this will be good. Just get any temptation out of our system. And we have the rest of our lives to be with one another."

"That does sound pretty good."

"Also, you can't tell me at least part of you is looking forward to tonight. One last chance to complete that fantasy you told me about."

"And you're good with that?"

"Yes," Hailee said and then kissed me. "I trust you completely, and based on this ring on my finger, I am pretty sure you feel the same way."

"I do."
____________________________________________________

THE NEXT DAY


Hailee and I had agreed that we would not contact one another until 5 PM unless there was a true emergency. That is why I was so surprised when at 12:30, someone was knocking on my door. The house was empty except for me as I cleaned things up. I thought there might be a slight chance that maybe it was Hailee back early and was knocking on the door to make sure she did not walk in on anything. When I opened the door, I found out that that was the case. Instead of Hailee's striking, beautiful smiling face, I was greeted by another beauty, Victoria Justice.

"Hi Eddie," she greeted me.

"Hey, Vee. What's going on?"

"Not much. Is anyone else home?"

"No, not right now."

"Great," she said as she entered my house. "So when does Hailee get back?"

"Five," I told her as I closed the door.

"Perfect, so we got plenty of time," She said happily. d"Wow, things must have gotten pretty wild after I left. Your place is trashed," the Trust actress said as she walked through my place, heading back towards the kitchen.

"Yup. I was just doing some preliminary cleaning, and then I have a maid service coming tomorrow afternoon." I spoke as I followed Victoria as she meandered through my place. "Look, VJ, no offense, but what are you doing here?"

"What am I doing showing up at your house when I was guessing you'd be alone just hours before you go fully off the market? And all this time, I thought you were so smart," she joked. "So tell me, did your night go as planned?"

"I didn't have a fully thought-out plan, but the night went well."

"Tell me about it," she said.

"What?"

"Tell me what happened."

"You want to know what happened here last night," Victoria nodded, so I thought for a moment before telling her a few things. "Let's see, well Kira Kosarin got caught by someone making out with the guy who was her secret hall pass while her boyfriend was in the next room. A ton of people heard Camila Cabello having sex since the bedroom windows were wide open. Someone walked on Stella Hudgens having sex in my laundry room. She bent over with the back of her dress flipped up, and supposedly she was caught smelling her own cream. Umm, Vanessa and her boyfriend got into a fight when she said the name of another guy she was fucking while they were having sex. And while he was storming out, she yelled something about how maybe if he came inside her for once, she wouldn't need to get any side dick." I paused and thought more about some of the wild things I saw or heard happen but did not include me much. "Oh, and when I was in the kitchen fingering Kat McNamara when we saw your sister and Katherine Laprell sneaking off together, I can only guess what they got up to."

"Just going to take a wild guess that the guy Stella was with wasn't her fiance."

"Considering he wasn't here, I highly doubt that it was. Honestly, I don't get those two. It's like they rather fuck other people than each other."

"Yeah, no one thinks they are going to end happily ever after. But forget all that. That's not what I meant," Victoria said, annoyed.

"It's not?" I said with fake surprise, and Vic gave me a look. "Oh, you mean you want to know who did I get with last night?"

"Yes!"

"All of the details?"

"We have the time."

"What do I get from telling you?" I asked, even though I knew I would tell her at least some things that happened anyway.

"You know what you get," she replied.

"You wouldn't be here unless I was going to get that regardless."

"Well, I'm sure I can think of some way to make it up to you."

"Alright, fine. Why don't we go out to the pool, and I'll tell you what you want to hear," I told her and then walked over to the refrigerator to get myself a drink. "Oh, but you have to leave all your clothes right where they are." Victoria just smiled and rolled her eyes at my request, but sure enough, she stripped off everything. Heading outside, I took a seat on the edge of my hot tub dressed in basketball shorts and a Miami Heat jersey. VJ followed me out, perfectly naked, and took a seat on the opposite side of the hot tub. She sat leaning back with her arms behind her and her legs shoulder-width apart, giving me a view of her exquisite breasts and clean, probably recently waxed, pussy.

"You get cleaned up like that for me or just for bikini season," I asked, referring to Victoria Justice's relatively normal small bush being gone.

"Still as cocky as the day we met," she replied.

"Victoria Justice is sitting in front of me, buck naked, wanting me to tell her stories about me having sex with other celebrities before she has fucks me. It'd be weird if I didn't have a certain level of swagger, right?"

She rolled her eyes before agreeing, saying, "Fair point." And then she moved on. "So come on, tell me about yesterday."

"Yesterday was fun. Hailee and I stayed in bed most of the morning, and once we got up, we started to clean up and put some things away just in case things got a little too crazy. We didn't want people knocking some stuff over and breaking it. Caterers started dropping off some tables and stuff around three, and food began to arrive around four, and thankfully they were all gone before five when some guests started to arrive. So you know, heaps of people greeting, people congratulating Hailee and me and saying how happy they are for us. That went on for a while, but I'll skip ahead a bit since you want the juicy stuff. I think it was almost six. A lot of people had arrived, and they were enjoying themselves. I was over here," I said, pointing to a spot across the patio, "when Madison Pettis asked to talk with me."


____________________________________________________

THE EVENING OF THE PARTY






After asking if we could talk privately, Madison and I went inside my house. I went to go into the back, but Madison wanted to lead me upstairs instead. I could not understand why we needed to go up there to talk, then it kind of dawned on me that she wanted to do a little more than talk, so I let her lead the way. As far as I knew, she had never been upstairs at my place, but she really seemed to know where she was going as she headed for one of the guest bedrooms.

"So, I heard a rumor," Madison said as she closed the bedroom door behind me.

"Yeah? What did you hear?"

"That you and Hailee are going exclusive after tonight."

"That's true," I informed her.

"So, that means as of right now, you're still available to be with other people?" she asked, a little embarrassed.

"Yes."

"Even if it might not be someone who you have hooked up with before?"

"There were no restrictions like that, so hypothetically I could be with someone new," I knew where this was heading, so I decided to cut to the chase. "Look, Madison, you want to fuck, right? Is that why you brought me up here?"

"I've just heard a bunch of stories other people told me about you, and I've also seen a few videos with you and others. And I've thought about it a bunch, and if this is my last chance, I don't want to miss out," she said while kind of rambling.

"Your boyfriend won't mind this?" I asked.

"I thought if you just laid back and I rode you, and you don't cum, then I won't be so much like we had sex as I was just masturbating and using your dick as a dildo."

"Wait, so, you are going to ride my dick until you cum, and then I'm just left hanging with an erection? What kind of offer is that?"

"I mean, you do get to see me naked and feel my pussy. That's not nothing." She was right about that, "Plus, don't worry, I have a plan to get you off as well."

"What's that plan?"

"It's a surprise, but I promise you'll love it," Madison said with excitement in her voice.

"That does sound tempting," I said. Madison then smiled, and before I could even give my full consent, she had whipped off her shirt and exposed her sizable caramel-colored tits with milk chocolate-colored nipples. Just like she had seen videos of me having sex through some other people, I had seen her naked in a few pics sent to me by other guys. However, those pictures didn't thoroughly do her justice. She then moved in towards me. She kissed my cheek and pressed her tits up against me. She started to push me back towards the bed and while she continued to kiss the side of my face and my neck. I turned my face towards her, but she stopped me before our lips could touch. "No, we can't. I'm just going to use you. You can't do anything to me."

"If you're that scared about cheating that you're setting up these weird rules, are you sure you want to do this?"

She hesitated for a moment. Then I felt her hand rub my bulge through my pants. "Yes," she sighed, "I'm sure." I then felt her hand tighten around me as she traced the outline of my hardened dick in my pants with her fingers. "Besides, I already know how I am going to make it up to him. He's told me how he's fantasized about my best friend [Torri Webster]. I've planned for her to spend the weekend with us next month. Once he finds out about that threesome, he won't care what I've done," she said as she pulled off my shirt.

When my legs hit up against the bed, I sat down and pushed myself towards the middle of the bed. I watched as Madison undid her jean shorts and pushed them down her legs, along with her thong. Now left standing in nothing but some strappy heeled sandals, she pulled off my shoes and then climbed up onto the bed. The beautiful actress straddled my thighs, and with her legs spread like that, I had a perfect view of the shaved wet pussy that I would soon be stretching out with my hard cock. My view then got blocked as her hands got in the way as she reached out to undo my pants.

"Oh wow," she said as my manhood flopped out of my pants. She dragged my pants and underwear down, and I pulled off my shirt. "It looks even nicer than it does in the videos," Madson said as she took my dick into both her hands. She stroked me for a bit, with her eyes captivated by the man meat in her hands.

When she finally looked away, she looked up and met my eyes and gave me a big smile. Our eyes did not lock for long as she quickly moved her eyes back down and opened her mouth, and placed my dick against the tongue. Madison swirled her tongue around a bit before taking the tip into her mouth and giving it a suck. Madison toyed with my dick a bit, feeling it, stroking it, seeing how much she could get down her throat. However, she only did that for a little bit and quickly changed to licking the sides of my shaft and making sure my cock was nice and slick with her saliva. When she was satisfied my cock was nice and lubed up, she got on top of me and straddled my waist. Taking my dick and pointing up towards the ceiling, she rubbed her slick lower lips up against it.

"I can't believe we're finally going to do this," she said before finally pushing my tip towards her opening. She gasped as she felt herself being slit open as she settled herself down on top of my dick. "Oh wow," she said as she stopped about halfway down.

"You alright?" I asked with some concern.

"I'm better than alright; you're just wider than I am used to," She informed me. She stayed in that same spot a bit, letting herself adjust the sizable object now penetrating her. When she moved again, she lifted herself up a bit and then moved down another inch and a half. I wanted to grab her hips and pull her down or thrust my hips up to fill her up entirely, but I had said that I would not do anything, and I was planning on keeping my word. As she started moving more, she moaned out, "Feels so good."

Madison may have started slow, but she did find her rhythm as she bounced on my dick. With her hand resting on my chest, I laid back and watched her enjoy herself on top of me. Like any man, I found her breasts to be hypnotic as they bounced. I got excited when Madison changed up her method from bouncing to grinding. Now instead of sitting up, her body was leaning over mine. Her big tits now hung right by my face. I could not help myself from grabbing hold of both of them and bringing one up to my mouth. She loved the added sensation of my lips wrapped around her tit, sucking on her nipple. She let out several loud moans and muttered a few words, informing me how much she liked it.

"Wait, wait, wait. You have to stop," Pettis spoke up and said with some frustration.

"Why?"

"Because no touching, remember. You can't be playing with my boobs like that."

"But you like how it feels?"

"Yes, it feels amazing." I let go of her tits and laid there for a moment as she continued to ride me. Finally, an idea popped into my head.

"What if I was just laying here with my mouth open, and your tit just happened to enter my mouth. Would that violate the rules?"

"No, I don't think so," she said with a big smile. Did it probably violate the rules she set out? Yes. Did either of us care at the moment? No. So I moved a few pillows behind me to prop my head up, and Madison now moved her body so that as she moved along my hard pole, her breasts directly rubbed up against my face, and I would suck and bite down on her nipples periodically.

"Such a great dick," the He's All That actress said through gritted teeth. She was now working herself faster and faster on my dick, slamming herself down hard each time. Finally, she let out a loud moan that turned into a cry as her orgasm overtook her. I could feel her pussy quiver, and Madison got even wetter as she achieved her goal of cumming on my cock.

"Of fuck, me," Madison sighed as she came down from her organic high.

"Enjoy yourself?" I asked as she stayed sitting on top of me with my erections still inside her, soaking in her fresh squirted juices.

"Yeah, I did. So glad we did that," Madison replied, moving her hair out of her face. "I wish we could do more," she said, rolling her hips a bit.

"Speaking about doing more," I said as I thrust my hips up into her.

"I guess I should get off of you and let someone else finish you off before I give in and let you take me," Madison said, circling her hips two more times before climbing off of me and turning to the closet. She then called out, "Okay, Nat, he's all yours."

Suddenly a bouncy, bubbly blonde came barging out of the closet and bounded onto the bed. The short buxom woman handed the phone in her hand over to Madison. "Her, take this and keep recording."

"What? You were filming us?" Madison said with surprise as she was forced to take the phone into her hands.

"Yes. Now it's your turn to film me," Natalie told Madison before turning back to me. "Hi," Nat said to me with a big smile and pulled me into a deep kiss with both her hands.







"Hi Nat," I said when Natalie Alyn Lind finally let go of my face. Natalie was completely naked as she sat on top of me with my dick resting against her ass. Judging by the slime trail she was leaving on my stomach and how wet one of her hands was when she grabbed my head, it was apparent that she was also touching herself while in the closet. "It's been a while.'

"Too long," Natalie said. While I had been talking about the fact that we just had not physically seen each other in months. Nat meanwhile let it be known that she meant something entirely. "I wanted to give you a call when Jordan and I split, but I heard you were living with Hailee in New York," she said, then kissed me once again, only to continue once she pulled away again. "I thought you two had gone exclusive. When I heard that you were on the market for one last night, I knew I had to get you one last time." She then bent down and whispered into my ear, "I missed your cock."

Natalie kissed my neck. With how worked up she was, I might have been worried she could leave a hickey, but Hailee had purposely left it on that side of my neck that same morning. She wanted to let it be known, regardless of what happened; I belonged to her. As Natalie kissed me, she reached behind her and took hold of my shaft. Nat began inching her body back until my tip touched her moist slit. She pulled away from the crook of my neck and looked at me with an eager smile. Natalie then lowered herself down and sheathed my manhood inside of her. If I had any question about whether or not she was touching herself in the closet, those doubts were washed her way by how soaking wet her tight box was.

"I missed this," Nat said as she rocked her body back and forth on my dick.

"I missed these," I said as I reached up and grabbed onto Natalie's breasts. I had been watching them sway as Natalie fucked me, just like I had been with Madison, but unlike Madison, I was now allowed to play with them. I played with them in my hands before I wrapped my arm around Natalie's back and pulled her down to me. The Tell Me A Story actress was now smothering me with her breasts as she continued to grind herself into my dick. My mouth worked one sucking one of her nipples, and I moved one hand down to grab her ass. Natalie soon began to up her pace, going from a slow grind to a hard bounce on my dick.

‘Ugghh, I'm going to cum on your dick. I'm going to cum all over your big fat dick." Natalie yelled out. I felt movement on the bed behind me, which briefly broke my concentration on Natalie. Looking back, I could see it was just Madison moving around on her knees behind me. She was pointing the camera straight at Nat's face. My attention was brought back to the busty blonde when I felt the pussy clench around my dick. As she began to cry out in ecstasy, I noticed that unlike how she usually looks me in the eye as she climaxes, Nat was instead looking directly at the lens of the camera. I did not choose to fuck her as she orgasmed. Instead, I just laid back and let Natalie ride her waves of pleasure. Once she died down, I wrapped her in my arms and spun us over so that Nat was on her back.

"What are you doing," Madison asked as she watched me, through the camera on the phone, pull out and get off the bed.

"This is over when I finish, and I am not ready to finish yet," I told her, and I grabbed Natalie's thighs and pulled her down to the edge of the bed. If I wanted to, it probably would have only taken me a minute to get myself to pop off into Natalie, but that's not what I wanted. Instead, I was buying myself some time and letting my dick back away from the edge by eating out her clean shaved snatch.

"Ummm, I've been dreaming about you dick so much I forgot how good you can be with your mouth," Natalie said as I worked my lips and tongue on her.

"Is he actually good at it?" Madison asked.

"Oh yeah, you missed out," Natalie teased.

"Can't say I got talent, but it turns out just putting in effort when you eat out a woman goes a long way," I said. I then gave Natalie's pussy lips and nice long lick before adding, "It also helps that we've done this enough that I know what Natalie likes."

"Yeah, you do," Natalie said as she wrapped one of her legs behind my neck, and I went back down between her thighs. I only used my mouth for the first minutes, drinking in the fresh juices of her recent climax. I was surprised once I added my fingers into her and locked my lips around her clit, just how quickly she was once again having a spasm of pure bliss.

"So, you two going to fuck now?" Madison asked when I moved my face out from between Natalie's thighs.

"No, not yet," Nat said before I could answer, "And I want to make sure you get a perfect shot of this." Natalie instructed me to sit on the edge of the bed. She moved off the bed and down to her knees on the floor. Nat directed Madison to move next to me and point the camera down at her. As the Big Sky actress wrapped both her hands around my dick, she double-checked with Madison that she had a good view with the camera. The beautiful blonde turned her attention back to me when Madison said yes. She looked up into my eyes and gave several rapid flicks of her tongue to the underside of my dick before gathering spit in her mouth and then dripping it onto my mushroom head. She used her hands to spread her saliva along my shaft. She spit and spread two more times, making sure my dick was nice and slick. When satisfied, she raised higher and moved closer to me on her knees. Nat then wrapped her large breasts around my dick. She clutched her breasts tightly as she began moving her body, giving me an excellent steady tit job.

"Oh wow," Madison said softly. The words unintentionally escaped her lips.

"Does it look good?" Natalie asked as she looked over at the other woman in the room. Or, more precisely, looking right at the lens of the camera in her hands.

"Yeah, it does," she answered. Happy that it did, Natalie gave a big smile to the camera and then a wink. The reason for the wink became evident while continuing to stroke my shaft with her spectacular breasts. She moved to begin licking the tip of my dick while doing so. While that felt good, it was only a tease when compared to when she wrapped her lips around the head of my cock as it stuck out over the top of her breasts.

"Holy fuck," I grunted. Not able to hold back on how incredible Natalie was making me feel.

"That's so hot," Madison let Natalie know as she continued to film everything. Now she was only holding the phone with one hand, as her other was toying with her sex.

"You wanna try it," Natalie offered. "You'd be doing it to him, so it doesn't break your dumb rules."

"True," Madison said as she thought about it. Natalie used that time to release my dick from between her breasts and add a fresh spit coat to my dick. "Okay, let me at it."

Natale took my dick into her mouth as Madison moved to the floor and took position next to her. The two naked beauties decided to give me the camera to film everything. As I took hold of the camera, Natalie slipped my dick from her mouth and pointed it right at Madison's face. Pettis quickly opened wide and took me into her mouth. As she sucked me, Natalie began kissing the side of my shaft. The two worked in tandem before Natalie backed off and let Madison take the center position. She wrapped her soft, light cocoa-colored breasts and proceeded to give me a tit job of her own. Rather than just moving her breasts or torso, Madison seemed to bounce her whole body to stroke me between her large pillowy tits.

Madison enjoyed giving my poll a thorough polishing with her fun bags. She tried to emulate Natalie and lick my tip while it stuck out over their breasts. Madison was starting to work my tip with her mouth when Natalie jumped up and announced, "Fuck this, I can't take it anymore."

Natalie hurried to the middle of the bed. Laying on her back, she spread her legs wide with her knees up. "Fucking pound me. I want it to feel like you're still inside me when I wake up tomorrow." I pulled my dick out from between Madison Pettis' amazing breasts. I still had the phone in my hand and decided to do a nice tight close-up scan of her body, making sure you could see her entire naked body in detail before handing the phone back over to Madison, who had joined us on the bed. I moved between her legs, and as I brought my manhood close to Natalie's very eager twat, Nat wrapped her legs around my back.

I bent down to kiss Natalie, and as our lips locked, I pushed my hips forward and pushed my cock right into her. Nat let out an excited squeal as she felt herself getting penetrated. I then sat back up, lifted one of her legs, and rested it on my shoulder. I slowly pulled my cock all the way back to just my tip and then plunged my entire length into her. Natalie let out a pleasurable groan at that. She gripped the bed and let out a similar moan as I did the same thing again. From there, it was on. I moved faster. Pistoning my dick in and out of her while playing with her breasts or rubbing her clit. Natalie, at one point, pulled me down to kiss her and clawed up my back a bit with her nails as we kissed and fucked.

"Damn, this is so hot," Madison piped up as she continued to film us while once again fingering herself as she watched. But while she was there, neither Natalie nor I were paying attention to her. We were two busy fucking one another. Nat had never hidden the fact that she liked me, nor how she really enjoyed having sex with me, and I never hid the fact that I genuinely enjoyed being in bed with her. So now, with this being probably our one last bang, we were making the best of it. She had both her hands bent back over her head and had a firm grip on the mattress while she arched her back upward. She was pushing her breasts up towards my mouth. Soon I was sucking in one of her breasts and a hand on the other.

Meanwhile, I was rapidly thrusting as hard and fast as possible. We had the bed shaking with the way we were fucking. She once again had her legs wrapped tightly around my back. Locking me in place with nowhere to go until she got off/

"I. Love. Your. Cock. I. Love. Your. Cock." Natalie said with each thrust as she built up to her orgasm. She finally burst and yelled, "I love you!" as she came the hardest she'd cum yet. Her body shook, and pussy gushed. Seeing and feeling Natalie cum one more time was just what I needed to bring me up to the edge.

"Almost there, Nat," I warned her. "I'm gonna cum on your tits."

"Yeah? You going to cover my tits in cum?"

"Oh yeah," I knew Natalie probably wished I would explode my load inside of her, but I had gotten the okay to do that to a few select women by Hailee, and I was not going to mess that up. The next best thing, of course, outside of cumming in her was to paint her face and breasts, especially with the whole thing being recorded.

"Alright, fuck, get on your knees," I said as I pulled out of Natalie and got to my feet, and Nat sprung up to her knees. We were both surprised when Madison moved over and took a spot on her knees.

"I need to be part of this," Pettis told us. The two of them were now both on their knees and pressed up close to one another. Madison had her arm extended out like she was taking a selfie to record the grand finale. I beat my dick for a minute until I finally erupted. It was my first load of the night, and you could certainly tell by the amount that came out. I just kept on firing as my jizz splashed both women's faces and tits. The amount surprised both of them so much that they started laughing about it as I finished up.

"Oh my god, is it always that much?" Madison asked.

"Not, normally. That was a bit extra," I told Madison.

"That was definitely in the top 3 or 4 amount I've seen Eddie cum when we've been together."

"He's cum more than that before?" Madison asked as she wiped a bit off her face.

"Yeah. I can't even imagine some of the loads he must give Hailee," Natalie said. She then proceeded to lick some of my cum off of Madison's cheek, which made the Five Points actress laugh.

Natalie used the bedsheets to wipe herself down a bit and then went to the closest to grab the clothes she had stripped off. Natalie and I both got dressed while Madison laid back in the bed.

"Madison, you okay?" I asked when fully redressed.

"Yes. I'm just going to stay here for a bit," She said. "I am so happy we did this. Glad I no longer have to wonder about all those stories."

"Yeah, that was great. You're amazing."

Natalie and I then both left the bedroom, and I made sure to shut the door because I was pretty sure she was about to rub one out. Natalie then reached up, pulled my face down to hers, and gave me a deep passionate kiss. Her tongue was deep into my mouth. When she finally let go of my face, I had to catch my breath.

"Eddie, I'm so happy we got to do this one last time," she said before giving me another, though lighter, kiss. "I'm happy for you and Hailee, and I hope you two stay together forever, but if you two ever break up, I want to call dibs on being the first one you rebound with."








____________________________________________________

"That's kind of sweet, but also maybe a little Fatal Attraction-ish," Victoria said in response to what I told her Natalie said.

"It's fine. Nat is harmless and sweet. Though Hailee might give her the stink eye next time she sees her."

"You're really going to tell her what she said?"

"Only way this whole thing works is if I do," I told her.

"That sweet that you two are so open," VJ complimented. "Though, I never pegged you as a big tits guy."

"I'm not, really. I generally prefer ones like yours or Hailee's, but when in Rome," I said with a shrug. "But it's not like either of them have overly huge or saggy ones. Madison and Nattalie both have some pretty spectacular tits."

"I guess so," she said. I grabbed my phone and opened up a picture of a topless Natalie that I still had on it. I then handed it over to Vic to have a look. "Oh wow, okay, those are actually really nice."

"Not quite as perfect looking like yours, but still pretty great," I complimented the actress as I took the phone back. "Besides, if I was purely interested in big tits, I doubt I would have much interest in Sabrina Carpenter."

"You did Sabrina in the ass last night?"

"Who said anything about her ass?" I questioned her.

"Please. If you did Sabrina, you did her ass. That girl's an anal freak."

"True, but you're not totally right either," I told her.


____________________________________________________






About two hours after my encounter with Madison and Natalie, my next one happened. Everyone had arrived, the house was packed, and the party was in full swing. I was just getting out of the bathroom when suddenly I was pushed back in by four hands.

"Hey, what the hell are you two doing?" I asked as I was pushed back into the bathroom.

"Shhhhh, we're trying to be secretive," Sabrina Carpenter said with a slight slur in her voice and the smell of alcohol on her breath.

"Yeah, be quiet," Joey King added as she shut the bathroom door and locked it with us inside. The two of them positioned me into the bathroom and had me take a seat on the closed-lid toilet. Looking at the two BFFs, it was easy to tell that they had both enjoyed themselves a few drinks since arriving at my home. They did not say anything right away.

"Okay, so you two plan on telling me what you're planning?" I asked, breaking the silence.

"We were talking about some sex stuff a few weeks ago, and then the topic of threesomes came up, and I wanted to know why Joey had never shared a dick with me," Sabrina filled me in. "I made her promise me that we'd at least give a double blowjob to some guy at some point."

"And then ten minutes ago, she told me she's picking you, and I don't break my promises," Joey added as Sabrina pulled the hand towels off the rack and put them down on the tiled floor for padding.

"What makes me so lucky?" I asked, though not really caring about the answer.

"You have a super nice cock," Sabrina said as she put her hand on it through my pants.

"And I don't want my boyfriend to think there is a chance of this becoming a recurring thing," Joey added as she got down on her knees beside her best friend. Sabrina quickly undid my pants, and I helped push them down to my ankles. Sabs quickly took my dick in her hands and started stroking it.

"That's what I'm talking about," She said as she just watched her small hand go up and down my shaft. She then bent my erection towards her mouth, quickly wrapped her lips around the tip, and sucked on my bell end. The only other time I had fooled around with Sabrina was at Olivia Holt's birthday in 2018. She and Sammi Hanratty gave me a double blowjob in my hot tub while Dove fucked her now ex-boyfriend across from us. She was kind of shy then, but now she was much more confident and really was the one taking charge. She sucked me solo for a minute before releasing my cock from her mouth with a loud pop and then pointed it at her friend. Joey looked at Sabrina and then up at me before opening wide and taking several inches into her mouth. While Sabrina had used her hand to stroke my shaft and kept her mouth only focused on the tip, Joey used no hands and bobbed her head, going down until she felt the tip hit the back of her mouth.

"Wow," Sabrina said in surprise as she watched her friend deep throat the long prick. "Where did you learn to do that?"

"Hunter taught me," Joey replied as she let the schlong escape her mouth, and she caught her breath.

"I should have known." Sabrina then took back over. The singer/actress tried to emulate her friend, going as far down the shaft as Joey could, but she struggled with that. Sabrina coughed a few times when she'd gone too far down.

"Maybe you should take off your shirts," I said to them as I noticed extra spit begin to leak down off my dick and down Sabrina's chin onto her shirt. "Don't want to make a big mess."

"You just want to see our boobs," Joey answered.

"It can be both," I snarky replied. Sabrina did not seem to care what the reason was since she discarded her shirt without saying anything. She freed her braless small tits and then looked at Joey to do the same.

"Fine," Joey said in reply to the look her friend was giving her. Joey took off her shirt and then unclipped her bra. As Sabrina wrapped her lips around my cock head once again, she also reached over and gave one of The Kissing Booth's star's tits a squeeze. While Sabrina's breasts were small with pink nipples that stood out, Joey's were more substantial with a bit of sag and darker reddish areolas. Joey then reached across and tweaked one of Sabrina's nipples. When Sabs lowered her head to take one of my balls into her mouth, Joey took the opportunity to suck my cock back into her mouth. It almost seemed like taking off their tops was very freeing for both. Where, with their shirts on, they were taking turns, not topless, they both worked their mouths on my dick. When Sabrina moved from my balls back to my shaft, Joey moved down to take a ball into her mouth. And when Joey moved her lips back up, Sabrina moved the tip out of her mouth and started licking and kissing the side of my member. Seeing what the Girl Meets World actress was doing, Joey mimicked her and worked the other side. It felt incredible having the two work seemingly as one. I paid close attention when they moved up my shaft until they were both kissing the sides of my tip. Then Sabrina reached behind Joey's head and pulled her into a kiss. Joey seemed a little reluctant at first, but she eventually just went with it. While technically it was just the two of them kissing, with my cockhead also right there getting the feeling of their lips and tongues, it was almost a type of three-way kiss.

"Okay, I gotta get this cock in me," Sabrina announced after breaking off her kiss.

"What? I thought we were just going to blow him," Joey said, questioning her best friend.

"Yeah, but you've fucked him before. From what I remember, it happened a bunch of times. All I ever did was fool around with him, once at a party with Sammi."

"She has a point," I said. They both looked up at me, with my dick still swinging between them. The look on their faces let me know that even though I was the guy they were talking about having sex with, I was not a part of this discussion. So they just looked at me for a minute and then continued with their own conversation.

"You liked having sex with Ed when you guys were doing it, right?"

"You know I did," Joey admitted, blushing slightly and knowing that she was going to be on the losing end of this argument.

"Then fuck you, it's now or never, and I am going to get mine," Sabrina told her as she stood up and moved over by the towel rack on the sidewall. Joey went back to sucking on my dick, getting it nice and wet as Sabrina then undid her shorts and pushed them and her underwear down to the floor. Sabrina bent over and grabbed onto the towel rack. She shook her butt at me teasingly as I pulled my dick away from Joey and moved over to Sabrina.

"Considering some of the things I've heard, I guess I should not be surprised," I said to Sabrina. I was, of course, referring to the metallic butt plug tipped with a blue crystal that was poking out from between her cheeks.

"Oh, you've been talking about me?"

"This is LA; you should know if more than two people know a secret, then everybody knows the secret," I said and then gave the plug a twist in her ass which caused her to moan. When I did try to go to fuck her, I did run into a bit of an issue. Sabrina was ready for me to take her from behind, but I stood over a foot taller than her, so my erection was practically at the middle of her back. So instead, I spun her around, and I picked her up in my arms. Sabs grabbed onto the trowel rack behind her as I speared her with my dick.

"Holy fuck," Sabrina yelled out as I penetrated her. Her chunky white sneakers pressed into my back as she wrapped her legs around me. Between how naturally small she was and thick my manhood is, it was a tight fit pushing my dick into her. But it was a tight fit in the best way possible. I was filling her completely, my dick rubbing every sensitive spot inside of her, and her pussy had a vice grip around my dick as I started bouncing her.

"Joey, I should divorce you," Sabrina said, referring to the fact that they often joke about being each other's wives.

"Why?"

"Because you should have been a friend and told me to fuck Ed a long time ago," Sabrina said as I continued to bounce her up and down my pole. She also enjoyed that my long fingers could play with the toy in her ass a bit as I bounced her up and down.

Sabrina and I were lost in our own world of sexual pleasure that we never noticed Joey had sat up on the sink counter with her skirt around her waist and had begun playing with herself. It wasn't until a loud moan escaped her lips, causing Sabrina and me to turn and see what she was doing. When I saw what Joey was up to, I pulled Sabrina away from the wall and sat her down right next to Joey.

"You dirty bitch," Sabrina said jokingly, "can't believe you're masturbating to us."

"You two are having sex right in front of me. What else am I supposed to do?" Joey asked.

"Maybe she'd like to join," I interjected. I pumped into Sabs two more times and then withdrew my cock. I took a step over to the side so that I now stood in front of Joey. I looked into the Kissing Booth actress' eyes. She did not say anything. Her only response to me standing before her with my hard rod pointing right between her legs was to move her fingers out of the way and spread her legs wider. Joey moved her arms behind her, and she leaned back on her hands. That was all the consent I needed as I moved forward, took hold of her hips, and impaled her on my cock.

"I'd forgotten how much I liked this; wow," Joey said as I fucked her on the counter. I pumped away at her for two minutes, then pulled out of her and moved back over to Sabrina to resume fucking her. I did not want to leave Joey hanging as I humped Sabrina, so I began fingering the youngest King sister. I alternated between the two best friends fucking one while fingering the other for the next several minutes. In no time, both my hands were soaked, and my cock drenched in juices from both of them. I was deep in Joey when Sabrina announced that she had a strong desire she needed me to fill.

"Okay, enough fucking around. Time to stick that monster in my ass," Sabrina said as she slid off the counter and extracted the toy from her backdoor.

"What!?" Joey yelled out. Both of us stopped screwing as it registered what Sabrina said. "No, you're not going to do that."

"Please, we both knew as soon as Ed and I started having sex how this was going to end."

"No, Sabrina. He's not going to fuck your ass and then stick his dick into my pussy right after." I just let the two bicker back-and-forth for a minute before I finally spoke up and gave direction.

"Okay, listen, this is what's going to happen. We are going to lay a bunch of towels down, and then Joey, you're going to lay back and let Sabrina eat you out while I fuck her ass," and then I snatched the butt plug from the former Girl Meets World actress' hand and held it up. "Then I am going to cum in Sabrina's ass and shove the toy back into her to keep my load deep in her for the rest of the party."

"That sounds wild. I'm in," Sabrina quickly agreed. Joey was a bit more hesitant. But in no time, I pulled out some spare towels and laid them on the floor, and Joey laid back and rested on her elbows. Sabrina then got down on her knees and elbows between Joey's wide-open legs.

"Looks like we're finally going to consummate this marriage," Sabs said to Joey before she lowered her face to her best friend's crotch. Joey took a deep breath as Sabrina began eating her out, but Joey started to moan in no time. I let them establish themselves before I moved into Sabrina. With her ass gaping from her toy and my cock still slick fucking the two of them, I did not give any warning as I started sliding my dick into her Sabrina's ass. You could hear a loud moan come from between Joey's legs. Sabrina's love of anal made things easy. There was no hesitancy or easing into things. Instead, we could go from 0-60 in almost no time. I was able to give it to her with full force, and she seemed to love it as she tried moaning and saying stuff in reaction to what I was doing to her ass, but everything she was saying was being muffled by it pressing against Joey's slit.

"Oh wow," Sabrina said as she finally lifted her face, "Why haven't we done this before?!"

"I know, right?" Joey moaned.

"I was talking about Eddie's dick. Fuck, he stretches my ass out sooooooo gooood," Sabrina cried out. "But you do taste nice too."

"Ok, well, I was talking about why I never let you eat me before," Joey replied and then pressed Sabrina's head back down to her pussy. The three of us kept going like that for several more minutes, with me fucking Sabrina Carpenter in the ass as she ate out Joey King. Sabrina was the first of us to orgasm and did so pretty soon after doing anal. Joey was the next one to orgasm. After she came, Joey backed off and just let her friend and I enjoy ourselves. We moved around, and I laid on the towels while Sabrina got on top of me and began riding me, anally, of course. And Joey moved back up to sitting on the counter watching us.

"Fuck I'm close," I warned.

"So am I," Sabrina moaned.

"I'm going to cum in your ass," I told her as I started to finger her pussy and rub her clit as she fucked her ass with my dick.

"You better do it. I want it. Give it to me," Sabrina said over and over again, telling me how she wanted me to blow my load in her ass. So I broke down and did just that. Pulling my fingers away from her hungry twat, I pulled her hips down and sank my cock balls deep inside the tiny actress and grunted as I began erupting.

"Oh shit! Oh, fuck!" Sabrina yelled out.

"Oh my god, are you squirting?" Joey asked with great surprise. When I moved my hand away from her clit, Sabrina replaced it with one of her own. She rubbed herself as I began cumming deep in her ass, and as a result, Sabrina came again. And Joey was right. As I was firing my load into her, Sabrina squirted out onto my stomach. The two of us came hard, and when we finished, Sabrina just sat on me with my dick still inside her rectum as we caught our breaths.

"Joey, toss me that toy?" I asked. She carefully picked it up and threw it down to me. I took the toy and flipped Sabrina and I over so suddenly Sabs was lying on her stomach. I then pulled off her and plugged her ass back up, keeping my spunk trapped inside her.

Now that we were done, the three of us jumped into the shower. We quickly washed the sweat and sexual fluids off of one another. We redressed, and the ladies quietly exited while I cleaned up all the discarded towels. Once the bathroom looked back to normal, I rejoined the party.







____________________________________________________

"I would have guessed Sabrina and Joey would have messed around before that," Victoria said.

"Yeah, I was surprised by that too. I would have bet big money on Sabrina having gone down on Joey before."

"Considering she and Rowan have, right?"

"I believe so," I replied. "I guess some women are not just into threesomes like you are. She just gave me a look before carrying on. Choosing not to respond to my comment about the number of threesomes she'd participated in.

"Any other rumors I might not know about get revealed at the party?" VJ asked.

"Ariana has a guy on the side. I guess she has kind of an open marriage since the husband doesn't like anal that much."

"I said something I didn't know. I'm pretty sure most people know about that. It's not a well-kept secret."

"Alright. Well, I didn't hear this last night, but I have heard some people talking about Gal Gadot having an open marriage, and she makes good use of that open policy."

"Shut up! No way," she said in total surprise.

"I don't have proof, just something that people were saying. You know that interview clip from the press for the first Wonder Woman movie where it looks like she eye bangs the fuck out of Chris Pine?" I asked.

"Of course."

"Well, I guess there is a chance that more than just her eyes did some banging."

"Wow, I never would have guessed that."

"Me neither. Though I bet, I can tell you something that did happen last night that you'll probably find just as surprising."

"I doubt it can be that surprising, but with that kind of build-up, you for sure have to tell me now."

____________________________________________________


It was about 10:30 pm when Hailee came up to me and told me that she would be heading out. We quickly excused ourselves, and snuck out into the garage, and got into the backseat of her car. We just wanted to check in, make sure we were both okay with what was happening, and confirm what time she was supposed to be back home. She then kissed me goodbye.

"You know, I was thinking earlier that it was a party kind of like this that we first met."

"I remember that. I think I walked in on you and Paris."

"Kind of, but I remember thinking you were the hottest woman I'd ever seen."

"Awwww. I did look pretty good that day."

"Yeah, but my opinion hasn't changed since that day," I told her. And then I gave her a kiss. Next thing you know, she is on my lap dry-humping as we made out. I ended up reaching into her pants and started fingering her as I kissed her neck and nibbled on her earlobe. We did not exit the car until Haiz had cum on my fingers, and I'd given her a hickey on her neck, and she'd given me a second one on the other side of my neck.

After she got out of the car, Hailee went to find her friends, and soon she and several members of her squad left to go somewhere; they didn't tell me where. I noticed a few guys had seemed to have left the party as well, but still, the house was still relatively full of people, and the party continued as it had before. Most of the people were outside on the patio around the pool. When the singer of Skinny Dipping decided to go skinny dipping herself, several other people quickly joined in with Sabrina. Some in their underwear, some without.

It was about 25 minutes after Hailee left as I walked out of the kitchen. I was distracted, sniffing the scent left on my fingers from Hailee that I practically walked right into Bailee Madison. I tried to step back and give some space to pass by, but she stepped right back close to me.







"There you are," she said nervously and with her eyes shifting and looking around, "Ummm, can we go talk somewhere in private?" she asked. I said sure, and we went upstairs into the master bedroom. As we entered, I closed the door behind us as she went and took a seat on the edge of the bed. She signaled that she wanted me to sit down next to her. "So when I heard about tonight's party, I started thinking. I wanted to do something special, and I also wanted to thank you."

"Thank me? What do you need to thank me for?"

"For doing some of the things we've done. I've always been a good girl. With my boyfriends, we've only ever done it on, like, a couch or a bed; I never thought I'd have a threesome, I'd never let a guy I wasn't dating cum inside me or go outside naked in the middle of the day. And yet somehow I let you cum inside me in the middle of a threesome with Hailee, and a few days before that, throughout the weekend, we did it everywhere in your house, including outside in the middle of the day." I did remember that. Right before Hailee and I got together, Hailee called on a Saturday morning while I was hooking up with Bailee. I had made plans to meet Hailee later in the week, but Bailee stayed over the entire weekend. I refused to let her put on any clothes after they got taken off on Friday night, and that included when we went outside to the hot tub. We went at it like rabbits, including doing it out up against the fence that separated my yard from my neighbors as we could overhear those same neighbors having a party on their side of the thick wood fencing. "I mean, heck, the first time we ever met, I let you finger me, and I was a half-second away from giving you a blow job while we were at a gym. So I just wanted to do something special as a thank you for letting me be kind of a wild girl for a change."

"....and?" She was holding something else back. I could just see it in her face. She was thinking in her mind but didn't want to say it aloud.

"And what?"

"And what else? I get it you want to do something special and stuff, but there is something else. Something you both want to say but also don't want to say out loud." I inched closer to her, and we just looked directly into one another's eyes in silence. I knew she would break first. It took a minute, but she broke.

"I need you to fuck me again. I need to feel your dick inside me one more time," she blurted out at a million miles an hour.

"See, that was easy, and sure I'd like that a lot too," I told her.

"Good, but that's not the special thing I wanted to do."

"Then what's the special thing?"

Bailee blushed and looked away from me. She could not look me in the eye as she said, "I want you to do me in the butt. I've never done it before, and I just thought about some of the other things we've done, and with this being one last time, I wanted you to be the first one who does it."

I was stunned. I never in a million years would have thought Bailee would ever want to try anal. Never mind, let me be the one to take her anal virginity. "Are you sure you want me to do it and not your boyfriend or like your future husband? Or some guy that might be, well, smaller than me to be your first?"

"No, I trust you, and I like you. And when I mentioned to a friend that I might be interested in trying anal, they had me talk to Sabrina about it, and she kind of got me prepared and let me practice using some of her butt plugs."

"Do you have one of them in right now?" I asked. Bailee nodded that she did. "Can I see it?

She stood up, and with her back to me, she lowered her leggings and bent over. There it was, in the middle of her ass, a circular black handle—a handle to the plug that was lodged inside of her innocent virgin ass. I could not help myself from reaching out and giving it a slight tug and a twist which caused her to groan. I then quickly spun her around and dropped to my knees. Now bending over the bed, Bailee moaned as I began licking her ever moistening pussy. Her pussy lips, which I could feel with my mouth, were recently waxed, but with my hand, I could feel the patch of trimmed hair just above her pussy. I lapped away at her tasty snatch for a minute before replacing my tongue with my fingers. "Are you serious about wanting to try anal?"

"Yes," she said as she flipped her hair over her shoulder and looked back at me.

"Then we're going to make sure you're very relaxed and not tense, and we need to make sure my dick is nice and wet. There are a few ways we can do that," I informed her.

"Is one of those ways with me cumming on your dick?" she asked.

"Yeah, that might work."

"Then let's do that," she said with a great deal of excitement. She was also extremely eager. I didn't even have my dick out before she had spun around and laid down on the edge of the bed, putting her feet up onto my shoulders. She'd done it so quickly that she still had her leggings hanging off one of her ankles. I lowered my pants, and as I moved closer, her angled legs moved higher and higher in the air until her body was at a near 90° angle with my hard dick resting right on her lower limbs. Moving my hips back and forth, I got my dick nice and wet from her juices. It also got Bailee breathing heavier as I rocked my body. I also tried to make sure I brushed my tip over her clit. I did that until I had her pleading, "Please. Stop teasing me. Just put it in me. Please!"

"What do you want me to put where?"

"Really?"

"Yes," I told her. Bailee always came off as such a good girl in public, and in most of her roles, I loved hearing her speak dirty things from time to time.

"Ugghhh… I need to put your huge dick in my pussy and fuck me!" she yelled. That put a smile on my face as I pulled back and got into position. I wrapped my arms around her thighs and pulled her towards me while thrusting my hips forward. Bailee gasped as, in a moment, she went from aching to be penetrated to having her pussy stuffed with my entire cock. It'd been a while since the two of us had done this, and it felt good to be back inside of Bailee Madison.

"Take off your shirt," I told her as I pistoned in and out of her and made sure to use my hand to rub her clit. I wanted to make her cum to have her relaxed before we tried anal, but I also wanted to make sure she came before I got too worked up from fucking her.

"I've missed your dick," Bailee said as she pulled off her shirt, exposing her braless tits that now wobbled each time I pushed into her. "I love the feeling of how you stretch me out, hit those deep spots inside of me. Hailee is so lucky."

Listening to Bailee's confession was a real turn-on. I was thankful I had already cum a few times already, or I might have filled her with my spunk too early. I knew she could not be too far from orgasm by her breathing, but I wanted to have a little fun with her. I reached and took hold butt plug handle that was still inside her. Bailee's eyes went wide when she felt me pull on and twist on the sex toy. I did not pull it hard enough to pull it out of her, but just hard enough that she could feel a slight pull coming from inside of her ass. I played with the toy in her ass for another minute before finally pulling it out of her. She let out a gasp in relief after the toy was out of her, and she gasped again as I went back to rubbing her clit as I pounded into her.

Bailee tried to pull my shirt to get me on top of her. But instead of falling on top of her, I pulled back and lifted her off the bed. I knew she was close to cumming as I cradled Bailee in my arms with her legs up over my shoulder. I rocked her body along my dick, and she began moaning loudly. Soon after that, Bailee announced that she was cumming, and her body shook in pleasure. After she came, I put her down on the bed.

"My pants," she said while still trying to shake her post-orgasmic haze, "I have some lube in my pants."

Going into her pants, I found a small bottle of lube in one of the tight pockets. She was lying in the middle of the bed as I grabbed the lube. Once on the bed, she quickly sat up and took the small bottle from me. Though still slick with her pussy juices, Bailee poured some lube into her hand and then rubbed down my cock. When she finished, I told her to roll over and lay down. I took a pillow and placed it under her hips so I'd have a good angle when I finally did penetrate her virgin ass. I squirted some lube onto her, and she moaned when I began messaging her ass, and then gasped, and I stuck a finger into her ass.

"How are we going to do this," she nervously asked as I fingered her ass.

"Remember that prone bone position we've done before? Just lay like you are, and I'll take care of the rest," I reassured her. When she was comfortable and ready to go, I tossed the bottle and got into position. Straddling her legs, I moved in behind her. She clenched up a bit as I rubbed my tip against her rosebud.

"You gotta relax and stay calm. Trust me and just relax," I told the brunette actress. She took a deep breath and unclenched a bit.

Despite just coming down from a powerful orgasm and both of us being adequately lubed up, fitting my did into Bailee's ass was like trying to fit the top half of a champagne cork into a wine bottle. She was gripping the sheets tightly and let out a painful grunt as I pushed forward until finally, the head of my cock slipped into her backdoor. I drove forward another inch before stopping, letting her ass get accustomed to having me inside of her. When she gave me the go-ahead, I slid a little deeper into her and then pulled back to the tip and slowly pushed forward again. Bailee did not seem entirely comfortable as I slowly dragged my dick in and out of her, but when I asked her if she wanted to stop, she refused on multiple occasions. As I went deeper and deeper into her rectum, I was happy that Bailee did seem to get and take advice from Sabrina on anal as my dick was coming on clean whenever I pulled my cock back.

"God damn, Bailee, and I thought your pussy was tight the first time we fucked," I told her.

"I was nice and tight until you stretched me out with your huge cock. Now you're stretching out my ass. It feels like you're going to split me in two."

"You want me to slow down?"

"No, keep going," she told me. "It kind of hurts, but it also feels good."

I began picking up speed, and as we kept going, Bailee relaxed more and more, and soon she was moaning in pleasure. I reached out and took one of her arms, and brought it towards me. I could take her hand into mine with her arm backward and then slid it down under her. With her hand now resting on her snatch, Bailee underwood what I was trying to get her to do. I could feel her hand starting to work her own pussy as I fucked her ass. Her moans now became longer, louder, and more excited. I wasn't sure I could make her cum from anal, but I was trying my best. Driving my cock down into her. Push her hips down into her hand, which was rubbing her clit.

"Bailee, I can't hold out much longer," I told her.

"Cum in my ass! Fill my ass with your cum!" she cried out as she humped her hand. Hearing a good Christian girl like Bailee call out for such a thing was too much. I let out a groan, and my whole body shuttered as filled up her ass with the contents of my balls.

"Oh wow! I can feel it. Oh my god," Bailee seemed to be simultaneously laughing and moaning as she felt her backdoor get injected with my spunk.

When it was all over, I slowly pulled out of her and got off the Pretty Little Liars: Original Sins actress. Once off, Bailee rolled over. Any doubt that I might have about whether or not she had actually enjoyed the experience dissipated when I saw the bright smile on her face.

"Wow, that was wow," she said with excitement.

"So you liked it?"

"Not as much as, you know, regular, but yeah, it was better than I thought it would be." She then just paused and looked at me. "We should take a picture to remember this."

Bailee got up and picked up her phone. She then got back into bed and climbed up right next to me. She pushed her breasts against me as she got close. She took a few pictures of the two of us smiling together, and while you could not see anything below our shoulders in the photos, it would be pretty evident to any third party who saw them that we were both shirtless.

"Okay, now stand up," she said.

"What? Why?"

"So I can remember the first cock I ever had in my butt," she said like that was an everyday thing. So I stood up. I was a little more than half mass when I stood up, so she stroked me to about 75%. She then posed with my dick pointing out towards her phone over her shoulder. Bailee took a series of photos like that. With a big smile on her face and my dick right next to her. The final picture was with her head turned, eyes closed, and her lips puckered as she gave the tip of the cock that had just been in her ass a light kiss.







______________________________________

"Oh my god, really? I never in a million years would have thought Bailee would ever do that," VJ said in reaction to my story.

"Neither would I, but it happened. As a goodbye gift, it's not a bad one."

"I'm not sure I can top that," Victoria said. I noticed the way she shifted as she sat there. As I told my stories, VJ could not help herself from reflexively giving one of her breasts a squeeze, rubbing her legs together, and occasionally dipping her hand between her legs quick moment here and there. As she continued to sit on the ledge, I noticed a small puddle forming underneath her, and it had nothing to do with the water from the hot tub.

"No one said you need to top it or do anything at all," I said.

"So, I have two questions. Who haven't you fucked you wished you did and is there anyone you didn't have sex with last night that you wish you had? Someone you had one final fuck with?" she asked.

"Present company excluded and not giving away what else happened last night, let me think. I never got with Miranda Cosgrove, and after being in the room while my stepsis watched all those iCarly episodes for years, it's hard not to have a thing for Miranda."

"It is hard," VJ jokes. Her double entendre refers to the fact that I had become hard while discussing my previous night's exploits. I just ignored her,

"And then, who do I wish I could have been with one last time?" I sat there and pondered a bit. "I'd have to say, Emma Watson. I would have loved to have had sex with Emma one last time."

"Why her?"

"Besides the fact that she is gorgeous and every guy my age would do horrific things to have a chance to bed Hermione Granger? Also, the way she likes to moan and whisper right into a guy's ear while doing missionary. Woof, I'm getting chills just thinking about it." As I spoke, I could see how VJ was shifting uncomfortably. She had an inch that badly needed to be scratched, so I moved towards her across the hot tub.







"What are you doing?" she asked as I moved between her legs.

"You're dying to get off, I can tell. And you're going to want a clear, undistracted mind for the last part of the night."

"How can you be so sure of that?" she asked, but as she did, she widened her legs, inviting me in.

"You know me. You know some of the stuff I've done. What if I told you that I pulled off one of my biggest fantasies? Or at least one of my biggest fantasies that doesn't include Hailee. And the real-world actions surpassed my imagination."

"That must be some wild story," she answered as I started to kiss her inner thighs. She then leaned back and spread her legs even wider. "I..uh, fuck, it doesn't even matter. I'm too worked up to turn down your tongue." she sighed. I then moved in and kissed her balded lower lips. Her scent overpowered the chlorine smell from the pool when I was kissing her thighs, and when my lips touched hers, I could feel right away just how wet she was. I ran my tongue up and down her folds before I wrapped my lips around her clit and sucked on it. She moaned as I began eating her out and being VJ; of course, she was as loud as usual. I lifted one of her legs to spread her wide. After a little bit, my knees started to get sore as they rested on the seat of the hot tub, and I am sure Victoria's elbows could not have been feeling great as she laid back on the stone patio. So I got up and took her hand, leading us over to the oversized patio lounge chair. She laid back on the comfy padded seat, and l moved back between her legs. I was licking and fingering the gorgeous Afterlife Of The Party star, building her closer and closer to orgasm, and getting her ready to listen to my final story from the previous night. By the end of it, the story would no doubt have her ready to jump me and give me a last ride to remember.

Sure enough, a few minutes later, with my lips on her clit and her hands on the back of my head, Victoria let out one of her orgasmic cries that I am sure that the neighbors on either side of my home could for sure hear. Even as she was in the throes of orgasm, I continued to fiddle with her clit with my tongue as her pussy drenched the two fingers I had inside her. When she was finally past her climax, I let her rest and catch her breath for a few minutes. I moved up the chair and took a seat next to Victoria. I checked to see if she was ready to hear my final story, and when she nodded yes, I told her how the night had ended.

"So before things concluded in my bedroom, there was one other minor thing that happened."


____________________________________






After my anal adventure with Bailee, I went into the master bedroom, stripped out my clothes, and went into the shower. I wanted to make sure I washed my dick clean before continuing the night. People knew to stay out of the master bedroom, so I thought I'd have a few minutes all to myself while the party continued in the rest of the house. I had only been under the spry of the water for a few seconds before my quiet shower was interrupted.

"There you are," I heard a familiar female voice say. Stepping out of the spray of the water and wiping water from my face, I saw Anna Kendrick standing in the doorway wearing a knee-length summer dress and white sneakers.

"Hey, Anna. What's up?"

"I was planning on leaving, but I wanted to find you and say goodbye before I leave." She then paused for a moment. "Though, now that I'm up here, I'm thinking I could use a shower before I head home," Anna said. She then reached behind her, undid the dress's back, and then pushed it to the floor. The short brunette was just in her sneakers and panties as she walked towards the shower, but she was totally stripped of any clothing when she reached the shower stall door. I made room for the short Pitch Perfect star as she got in the shower with me.

"So, how are you liking your party? You having fun?" Anna asked playfully.

"Yeah, I guess you could say that."

"Does that mean you're making the most of the last night of your open relationship?" she asked as she wrapped her tiny hand around my manhood.

"Well, there is a reason why I was taking a shower alone in the middle of a party."

"Came in here to wash off your dick, huh?"

"That was the plan, but you interrupted me before I even reached for the soap." As I spoke, Anna maintained eye contact with me while slowly stroking me. As I began to stiffen with the effort, her eyes dropped down to below my waist.

"I wonder if I'll be able to guess who it is," Anna said as she bent down. Being almost a foot taller than her, Anna only needed to bend her knees a bit and bend over at the waist to get my dick in her mouth. Wrapping her lips around my engorged cock head and sucking on it. "Oh my god, did you just fuck someone in the ass?" she asked after she popped my dick free.

"Yeah, I did. Bailee Madison."

"Woah! Never expected her to be someone to take it in the ass."

"It was her first time."

"Her first time doing anal was with your mammoth cock? She's either really brave or dumb," Anna said before flattening her tongue against the underside of my cock and giving the shaft a long back and forth. She then wrapped her lips around me and continued sucking my dick, unconcerned that 15 minutes before manhood was lodged up another woman's backdoor. It's incredible, for how small Anna Kendrick is, what an accomplished deepthroater she is. She continued for a few minutes before I made her stop.

"Oh good, you're ready to fuck now," Anna said as she sprang up quickly and turned to face the glass wall.

"No, Anna, we can't. I can't cum. I kind of have to save up," I told her.

"What the fuck does that mean?" She asked. I told Anna my plans for the rest of the night and why I needed to keep a couple of bullets in the chamber.

"Okay," she said after I explained everything. "For the record, I'm not happy about this. It kind of feels like I'm getting screwed over, and not in the way I like it. But I guess I can understand from your point of view what you'd want that."

"Thank you, and just because I said I can't cum doesn't mean that you can't." I then moved Anna, so her back was against the wall, and I dropped down to my knees and spread her legs open by putting one up over my shoulder. I then pushed my head between her thighs and began eating her out. No foreplay or teasing; I just attacked her pussy with my lips and tongue. She was quick to put her hands on the back of my head and pushed me right into her crotch, rubbing my nose right into the tuft of hair she had just above her pussy.

"Mmmm yeah, eat that pussy. If we're not going to fuck, you better lick me good," she moaned as she made sure my head stayed between her legs. As I continued to go down on her, I reached up and took one of her breasts into my hand and began playing with her nipple. At one point, Anna told me to hold on to her hips as she took a tighter grip on my head. Now with more stability, she lifted her other leg. I had Anna suspended off the floor. Both her legs were sitting on my shoulders while her back pressed against the glass wall. She now had her legs crossed behind my head as I ate her out. Her moans were becoming louder, and her breathing was becoming more rapid. "Eddie, I need you to put your dick in me. If this is going to be our last time, I want to cum on that cock."

"Anna, you know…."

"I'm asking you to put it in me, not creampie me," Anna replied in frustration.

"Fuck it, fine," I relented. I started standing up, and Anna slipped her body down, her legs now going straight up in the air as they pressed up against my chest. I cupped her ass, and with her body wedged between my body and the glass at her back, I thrust forward.

"Ummm, YESSSS!" Anna called out as she felt her pussy get stretched and completely filled. It took barely three thrusts before Anna's body began to convulse, and she creamed all over my stiff rod. Though I had accomplished what the Pitch Perfect star wanted. Fucking Anna Kendrick just felt so good that I kept going. At first, as she continued her climax, I was just pounding her against the shower stall, but as her head cleared, we changed things up a bit. I was still holding up Anna, but she now had her legs wrapped around my back.

"I. LOVE. YOUR. COCK. I. LOVE. YOUR. COCK." The Simple Favor actress said over and over again, each time saying a word as she bottomed out while bouncing on my dick. She felt so good that I almost said fuck it to my future plans and gone all the way and finished in Anna. Thankfully, Anna had a surprisingly quick second orgasm, and with that, I was able to regather my thoughts and stop myself before I blew my load.

"Whoofff," Ana said as she grabbed on my arm when her knee buckled a bit as she got off of me and tried to stand on her own feet again. "Been a while since a guy's got my legs this shaking," she said. Not sure if it was true, but it was nice to hear. Once she got her balance, she made her way out of the shower, and I moved back under the spray. I focused back on myself until she called out to me again.

"Well, Eddie, I guess I'll get going now," Anna said after she dried off and put her clothes back on. I paused the scrubbing of my body to refocus back on Anna. "I hope this little fun helps deliver a massive cum shot to the next girl."

"I think that is very possible," I replied, considering I still had a raging erection.

"I'm gonna text Hailee that she is fortunate to have you, and not just because she's locking down that tongue and dick of yours."

"That's sweet of you," I laughed.

"Bye, Eddie."

"Night, Anna."


(To Be Continued)